WO1993008795A1 - Transdermal therapeutic systems containing crystallization inhibitors - Google Patents
Transdermal therapeutic systems containing crystallization inhibitors Download PDFInfo
- Publication number
- WO1993008795A1 WO1993008795A1 PCT/EP1992/002478 EP9202478W WO9308795A1 WO 1993008795 A1 WO1993008795 A1 WO 1993008795A1 EP 9202478 W EP9202478 W EP 9202478W WO 9308795 A1 WO9308795 A1 WO 9308795A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- transdermal therapeutic
- therapeutic system
- crystallization inhibitor
- active ingredient
- penetration enhancer
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
- A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
- A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
- A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
- A61K9/7046—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds
- A61K9/7053—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds obtained by reactions only involving carbon to carbon unsaturated bonds, e.g. polyvinyl, polyisobutylene, polystyrene
- A61K9/7061—Polyacrylates
Definitions
- the invention relates to transdermal therapeutic systems which make active substances available to the organism through the skin and which are characterized in that crystallization inhibitors are contained in the active substance-containing matrix.
- Transdermal therapeutic systems are known to be multi-layer plasters that are fixed on the skin and that continuously release the active ingredient percutaneously over a longer period of time.
- transdermal therapeutic systems consist of a cover film impermeable to water, penetration enhancers and active ingredients, a matrix that seals the skin pressure sensitive adhesive,
- therapeutic systems generally allow a high flow of active ingredients through the skin.
- so-called supersaturated has become more common in recent times
- crystallization inhibitors are added according to the invention (Fig. 1). By adding crystallization inhibitors, a high proportion of active ingredient remains dissolved during the storage period. The physical stability achieved in this way
- Transdermal systems are a basic requirement for application in practice.
- Crystallization inhibitors are incorporated, are characterized by very good in vitro drug delivery - as shown in Figure 2 using the example of 17ß-estradiol.
- a crystallization inhibitor such as silicon dioxide has a significantly lower tendency to crystal formation than a comparison TDS without silicon dioxide addition. While no crystal growth was found in the system according to the invention over the observation period of 8 months when stored at room temperature, large crystals ( ⁇ 730 ⁇ m) were formed in the system without crystallization inhibitors (Table 1). Highly disperse silicon dioxide or macromolecular substances are suitable as crystallization inhibitors.
- macromolecular substances are, for example, polyvinylpyrrolidones with an average molecular weight of about 1000-2 000000 (e.g.
- Polyvinyl pyrrolidones such as the Kollidon ® CL from BASF
- polyvinyl alcohol such as the Kollidon ® CL from BASF
- polyvinyl alcohol such as the Kollidon ® CL from BASF
- hydroxypropyl cellulose such as the Kollidon ® CL from BASF
- ethyl cellulose such as the Kollidon ® CL from BASF
- starch derivatives
- dextrins and dextrans such as, for example, ⁇ -, ⁇ - and ⁇ -cyclodextrin, dimethyi- ⁇ -cyclodextrin and 2- Hydroxypropyl- ⁇ -cyclodextrin
- sterols such as cholesterol
- bile acids such as cholic acid or lithocholic acid.
- Crystallization inhibitors can be used in all known transdermal systems, for example in polyacrylate systems or in systems based on silicone or synthetic rubber skin pressure sensitive adhesives, the inhibitor being incorporated in concentrations of 0.1 to 40 percent by weight based on the total weight of the matrix.
- the crystallization inhibitor can contain penetration enhancers, all known penetration enhancers and their mixtures being used in the usual concentrations.
- Suitable penetration enhancers are, for example:
- Monohydric and polyhydric alcohols with up to 24 carbon atoms such as 1,2-propanediol, 1,3-propanediol, 1,2-ethanediol, glycerol or lauryl alcohol; free carboxylic acids with up to 24 carbon atoms, such as lauric acid; Fatty acid esters with up to 24 carbon atoms in the fatty acid component and up to 20 carbon atoms in the mono- or polyhydric alcohol component, such as isopropyl myristate, glycerol monopalmitate, dodecanoyl acetate; Terpenes, amides, urea and mixtures of these penetration enhancers.
- concentrations of the penetration enhancers or the mixtures of the substance classes mentioned can be between 0.5 to 40 percent by weight based on the
- Preferred concentration ranges are 15-25 percent by weight for 1,2-propanediol, 0.5-15 percent by weight for fatty acid esters, free carboxylic acids and alcohols with 8-24 carbon atoms, and enhancer mixtures, which are possible in mixing ratios of 1:10 to 10: 1, for example for 1,2-propanediol and lauric acid, 5-40 percent by weight, preferably 20-30 percent by weight based on the finished matrix.
- Active substances which are suitable for producing the transdermal systems according to the invention are preferably those which are sparingly soluble or insoluble in customary adhesive systems and crystallize well, for example steroid hormones such as:
- Androgenic steroid hormones such as the 17ß-hydroxy-4-androsten-3-one
- Suitable active ingredients are also:
- Carotenoids such as ⁇ -carotene and ⁇ -carotene.
- ⁇ -carbolines such as the 5-isopropyl-4-methyl- ⁇ -carboline-3-carboxylic acid ethyl ester and the 5-isopropyl-4-methoxymethyl- ⁇ -carboline-3-carboxylic acid ethyl ester and further ⁇ -carbolines, those in the European
- scopolamine should be mentioned as a suitable active ingredient.
- transdermal systems according to the invention can also contain mixtures of these active ingredients.
- the optimal concentration of the active ingredient in the transdermal therapeutic systems according to the invention is naturally dependent on the type of active ingredient, its
- Concentration in the finished matrix is 0.1 to 10 percent by weight based on this.
- transdermal therapeutic systems are preferably designed in such a way that they consist of a cover layer which is impermeable to the penetration enhancers and, if appropriate, also to water, and one which adheres to the cover layer Active substance-containing adhesive matrix, which contains crystallization inhibitor and penetration enhancer and which consist of a removable protective layer.
- transdermal therapeutic system can be prepared by mixing a solution of the adhesive in a low-boiling solvent with the active ingredient or mixture of active ingredients, the penetration enhancer and the crystallization inhibitor, and applying the mixture in a film-like manner on an impermeable, peelable protective layer which is volatile Solvent removed by heating and covering the product obtained with a top layer.
- Suitable solvents for dissolving the adhesive are, for example
- low-boiling alcohols such as methanol, ethanol or isopropanol
- low-boiling ketones such as acetone
- low-boiling hydrocarbons such as hexane
- low-boiling esters such as ethyl acetate and mixtures thereof.
- This process can be carried out by spreading a solution or suspension of the active ingredient, the crystallization inhibitor, the penetration enhancer and the adhesive in a volatile solvent on a removable protective layer and, after drying, at about 60 ° C. to 90 ° C. with a plan impermeable cover layer is provided.
- All films that are commonly used in transdermal therapeutic systems are suitable as removable protective layers. Such films are siliconized or fluoropolymer coated, for example.
- 10 to 100 ⁇ ax thick films of PVC, PVDC or their copolymers EVA, polyethylene or polyester as well as their coextrudates can optionally be used as a transparent pigmented or metallized layer as a covering layer.
- the drug layer applied thereon preferably has a thickness of 20 to 500 ⁇ m.
- the active ingredients are preferably dispensed over an area of 5 to 100 cm 2 .
- transdermal therapeutic systems can also be designed to be considerably more complex than the simple matrix systems already mentioned (Yie W. Chien: “Transdermal Controlled Systemic Medications", Marcel Dekker, Inc., New York and Basel, 1987 , Dr. Richard Baker: "Analysis of Transdermal Drug Delivery Patents 1934 to 1984” and “Analysis of Recent Transdermal Delivery Patents, 1984-1986 and Enhancers "Membrane
- the largely gas-bubble-free mass is applied to a siliconized polyester film (peeling film: eg FDA-PET release liner) in such a way that after removal of the volatile solvent (ethyl acetate) at 65-75 ° C above 2 up to 3 minutes a uniform film of 100 g / m 2 is formed. It is then laminated with a PVDC cover film (Saran 18L, 30 ⁇ m from Dow Chemical, Midland, MI, USA). The laminate obtained in this way is divided into individual plasters of 2.5 cm 2 - 25 cm 2 , preferably 10 cm 2, area by means of a punching device and packed in aluminized bags. The patches stick to the skin after the protective film has been removed and can be used to replace hormones.
- peeling film eg FDA-PET release liner
- the largely gas-bubble-free mass is applied to a siliconized polyester film (peel-off film: for example FDA-PET release liner) in such a way that after removal of the volatile solvent (ethyl acetate) at 65-75 ° C above 2 up to 3 minutes a uniform film of 100 g / m 2 is formed. It is then laminated with a PVDC cover film (Saran 18L, 30 ⁇ m from Dow Chemical, Midland, MI, USA). The laminate obtained in this way is divided into individual plasters of 2.5 cm 2 - 25 cm 2 , preferably 10 cm 2, area by means of a punching device and packed in aluminized bags. The patches stick to the skin after the protective film has been removed and can be used to replace hormones.
- a siliconized polyester film peel-off film: for example FDA-PET release liner
- the patches are produced as described in Example 1.
- the patches are produced as described in Example 1.
- the patches are produced as described in Example 1.
- the patches are produced as described in Example 1.
- the patches are produced as described in Example 1.
Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE59208918T DE59208918D1 (en) | 1991-10-31 | 1992-10-21 | TRANSDERMAL THERAPEUTIC SYSTEMS WITH CRYSTALIZATION INHIBITORS |
JP50815093A JP3526864B2 (en) | 1991-10-31 | 1992-10-21 | Transdermal therapeutic system with crystallization inhibitor |
EP92922822A EP0610357B1 (en) | 1991-10-31 | 1992-10-21 | Transdermal therapeutic systems containing crystallization inhibitors |
CA002120599A CA2120599C (en) | 1991-10-31 | 1992-10-21 | Transdermal therapeutic systems containing crystallization inhibitors |
HU9401257A HU227531B1 (en) | 1991-10-31 | 1992-11-23 | Transdermal therapeutic systems containing crystallization inhibitors |
FI942011A FI110061B (en) | 1991-10-31 | 1994-04-29 | Process for the preparation of a transdermal therapeutic system with a crystallization inhibitor |
NO941593A NO307644B1 (en) | 1991-10-31 | 1994-04-29 | Transdermal therapeutic system with crystallization inhibitor |
GR970402873T GR3025237T3 (en) | 1991-10-31 | 1997-10-31 | Transdermal therapeutic systems containing crystallization inhibitors. |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEP4136057.5 | 1991-10-31 | ||
DE4136057 | 1991-10-31 | ||
DE4210711A DE4210711A1 (en) | 1991-10-31 | 1992-03-27 | TRANSDERMAL THERAPEUTIC SYSTEMS WITH CRYSTALIZATION INHIBITORS |
DEP4210711.3 | 1992-03-27 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1993008795A1 true WO1993008795A1 (en) | 1993-05-13 |
Family
ID=25908725
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1992/002478 WO1993008795A1 (en) | 1991-10-31 | 1992-10-21 | Transdermal therapeutic systems containing crystallization inhibitors |
Country Status (14)
Country | Link |
---|---|
EP (1) | EP0610357B1 (en) |
JP (1) | JP3526864B2 (en) |
AT (1) | ATE158181T1 (en) |
AU (2) | AU2895392A (en) |
CA (1) | CA2120599C (en) |
DE (2) | DE4210711A1 (en) |
DK (1) | DK0610357T3 (en) |
ES (1) | ES2106888T3 (en) |
FI (1) | FI110061B (en) |
GR (1) | GR3025237T3 (en) |
HU (1) | HU227531B1 (en) |
NO (1) | NO307644B1 (en) |
PT (1) | PT101019B (en) |
WO (1) | WO1993008795A1 (en) |
Cited By (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1995001167A2 (en) * | 1993-06-25 | 1995-01-12 | Alza Corporation | Incorporating poly-n-vinyl amide in a transdermal system |
WO1995009618A1 (en) * | 1993-10-01 | 1995-04-13 | Rotta Research Laboratorium S.P.A. | Transdermal therapeutic system containing octyl dodecanol as crystallization inhibitor |
WO1995018603A1 (en) * | 1994-01-07 | 1995-07-13 | Noven Pharmaceuticals, Inc. | Transdermal device containing polyvinylpyrrolidone as solubility enhancer |
WO1995022321A1 (en) * | 1994-02-18 | 1995-08-24 | Schering Aktiengesellschaft | Desogestrel-containing transdermal application agent |
WO1996005814A1 (en) * | 1994-08-20 | 1996-02-29 | Lts Lohmann Therapie-Systeme Gmbh | Oestradiol transdermal therapeutic system comprising hygroscopic additives |
WO1996020699A1 (en) * | 1995-01-06 | 1996-07-11 | Noven Pharmaceuticals, Inc. | Composition and methods for transdermal delivery of acid-labile drugs |
DE19526864A1 (en) * | 1995-07-22 | 1997-01-23 | Labtec Gmbh | Hormone patches |
US5702720A (en) * | 1995-12-22 | 1997-12-30 | Minnesota Mining And Manufacturing Company | Transdermal device for the delivery of flurbiprofen |
EP0836506A1 (en) † | 1995-06-07 | 1998-04-22 | Cygnus, Inc. | Transdermal patch and method for administering 17-deacetyl norgestimate alone or in combination with an estrogen |
DE19649535A1 (en) * | 1996-11-29 | 1998-06-04 | Lohmann Therapie Syst Lts | Process for the production of a plaster-shaped therapeutic system |
WO1998030203A2 (en) * | 1997-01-13 | 1998-07-16 | Jenapharm Gmbh & Co. Kg | Transdermal therapeutic system |
WO1999066908A1 (en) * | 1998-06-22 | 1999-12-29 | Rottapharm B.V. | Matrix-type transdermal patch for steroid hormones |
DE19829713C1 (en) * | 1998-07-03 | 2000-01-05 | Lohmann Therapie Syst Lts | Therapeutic system with the addition of pearlescent pigments |
WO2000006130A1 (en) * | 1998-07-29 | 2000-02-10 | Lts Lohmann Therapie-Systeme Ag | Estradiol-containing patch for transdermal administration of hormones |
US6024974A (en) * | 1995-01-06 | 2000-02-15 | Noven Pharmaceuticals, Inc. | Composition and methods for transdermal delivery of acid labile drugs |
WO2002003969A2 (en) * | 2000-07-12 | 2002-01-17 | Hexal Ag | Transdermal therapeutic system for highly dispersed silicon dioxide |
DE102010040299A1 (en) | 2010-09-06 | 2012-03-08 | Bayer Schering Pharma Aktiengesellschaft | Transdermal therapeutic systems with crystallization-inhibiting protective film (release liner) |
US8580281B2 (en) | 2008-02-27 | 2013-11-12 | Hisamitsu Pharmaceutical Co., Inc. | Medicated patch |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19500662C2 (en) * | 1995-01-12 | 2001-04-26 | Lohmann Therapie Syst Lts | Plaster containing estradiol and its use |
US5698217A (en) * | 1995-05-31 | 1997-12-16 | Minnesota Mining And Manufacturing Company | Transdermal drug delivery device containing a desiccant |
DE19629468A1 (en) * | 1996-07-11 | 1998-01-15 | Schering Ag | Transdermal therapeutic systems |
GB9720470D0 (en) | 1997-09-25 | 1997-11-26 | Ethical Pharmaceuticals South | Inhibition of crystallization in transdermal devices |
DE19843027A1 (en) * | 1998-09-19 | 2000-03-23 | Labtec Gmbh | Transdermal therapeutic system used for administration of sex hormones contains neohesperidin dihydrochalcone to inhibit crystallization of active agent |
DE10012908B4 (en) * | 2000-03-16 | 2005-03-17 | Lts Lohmann Therapie-Systeme Ag | Stabilized supersaturated transdermal therapeutic matrix systems and methods for their preparation |
MXPA03011910A (en) * | 2001-06-18 | 2004-06-03 | Noven Pharma | Enhanced drug delivery in transdermal systems. |
PT1670433E (en) | 2003-10-10 | 2012-02-08 | Ferring Bv | Transdermal pharmaceutical formulation for minimizing skin residues |
JP4914826B2 (en) | 2005-02-28 | 2012-04-11 | 久光製薬株式会社 | Transdermal absorption preparation |
ES2661767T3 (en) | 2008-02-27 | 2018-04-03 | Hisamitsu Pharmaceutical Co., Inc. | Adhesive skin patch and packaged product |
US20110189261A1 (en) | 2008-03-03 | 2011-08-04 | Hisamitsu Pharmaceutical Co., Inc. | Transdermally absorbable preparation |
ES2841138T3 (en) | 2013-09-11 | 2021-07-07 | Medrx Co Ltd | Novel base composition for adhesive tape agent |
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EP0208395A1 (en) * | 1985-05-16 | 1987-01-14 | Euroceltique S.A. | Transdermal delivery system |
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-
1992
- 1992-03-27 DE DE4210711A patent/DE4210711A1/en not_active Withdrawn
- 1992-10-21 JP JP50815093A patent/JP3526864B2/en not_active Expired - Lifetime
- 1992-10-21 AU AU28953/92A patent/AU2895392A/en not_active Abandoned
- 1992-10-21 EP EP92922822A patent/EP0610357B1/en not_active Expired - Lifetime
- 1992-10-21 DE DE59208918T patent/DE59208918D1/en not_active Expired - Lifetime
- 1992-10-21 WO PCT/EP1992/002478 patent/WO1993008795A1/en active IP Right Grant
- 1992-10-21 AT AT92922822T patent/ATE158181T1/en active
- 1992-10-21 DK DK92922822.9T patent/DK0610357T3/en active
- 1992-10-21 CA CA002120599A patent/CA2120599C/en not_active Expired - Lifetime
- 1992-10-21 ES ES92922822T patent/ES2106888T3/en not_active Expired - Lifetime
- 1992-10-29 PT PT101019A patent/PT101019B/en not_active IP Right Cessation
- 1992-11-23 HU HU9401257A patent/HU227531B1/en unknown
-
1994
- 1994-04-29 FI FI942011A patent/FI110061B/en not_active IP Right Cessation
- 1994-04-29 NO NO941593A patent/NO307644B1/en not_active IP Right Cessation
-
1997
- 1997-03-25 AU AU16529/97A patent/AU712692B2/en not_active Expired
- 1997-10-31 GR GR970402873T patent/GR3025237T3/en unknown
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EP0450986A2 (en) * | 1990-04-06 | 1991-10-09 | Sekisui Kagaku Kogyo Kabushiki Kaisha | A percutaneous-administration-type pharmaceutical preparation of nitroglycerin |
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Cited By (35)
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US5656286A (en) * | 1988-03-04 | 1997-08-12 | Noven Pharmaceuticals, Inc. | Solubility parameter based drug delivery system and method for altering drug saturation concentration |
US6024976A (en) * | 1988-03-04 | 2000-02-15 | Noven Pharmaceuticals, Inc. | Solubility parameter based drug delivery system and method for altering drug saturation concentration |
US6248348B1 (en) | 1993-06-25 | 2001-06-19 | Alza Corporation | Incorporating poly-N-vinly amide in a transdermal system |
WO1995001167A3 (en) * | 1993-06-25 | 1995-02-16 | Alza Corp | Incorporating poly-n-vinyl amide in a transdermal system |
US5919478A (en) * | 1993-06-25 | 1999-07-06 | Alza Corporation | Incorporating poly-N-vinyl amide in a transdermal system |
WO1995001167A2 (en) * | 1993-06-25 | 1995-01-12 | Alza Corporation | Incorporating poly-n-vinyl amide in a transdermal system |
WO1995009618A1 (en) * | 1993-10-01 | 1995-04-13 | Rotta Research Laboratorium S.P.A. | Transdermal therapeutic system containing octyl dodecanol as crystallization inhibitor |
WO1995018603A1 (en) * | 1994-01-07 | 1995-07-13 | Noven Pharmaceuticals, Inc. | Transdermal device containing polyvinylpyrrolidone as solubility enhancer |
EP1329225A3 (en) * | 1994-01-07 | 2003-12-10 | Noven Pharmaceuticals, Inc. | Transdermal device containing polyvinylpyrrolidone as solubility enhancer |
EP1329225A2 (en) * | 1994-01-07 | 2003-07-23 | Noven Pharmaceuticals, Inc. | Transdermal device containing polyvinylpyrrolidone as solubility enhancer |
US6221383B1 (en) | 1994-01-07 | 2001-04-24 | Noven Pharmaceuticals, Inc. | Solubility parameter based drug delivery system and method for altering drug saturation concentration |
WO1995022321A1 (en) * | 1994-02-18 | 1995-08-24 | Schering Aktiengesellschaft | Desogestrel-containing transdermal application agent |
WO1996005814A1 (en) * | 1994-08-20 | 1996-02-29 | Lts Lohmann Therapie-Systeme Gmbh | Oestradiol transdermal therapeutic system comprising hygroscopic additives |
US6024974A (en) * | 1995-01-06 | 2000-02-15 | Noven Pharmaceuticals, Inc. | Composition and methods for transdermal delivery of acid labile drugs |
WO1996020699A1 (en) * | 1995-01-06 | 1996-07-11 | Noven Pharmaceuticals, Inc. | Composition and methods for transdermal delivery of acid-labile drugs |
EP0836506B2 (en) † | 1995-06-07 | 2011-12-21 | Ortho-McNeil Pharmaceutical, Inc. | Transdermal patch for administering 17-deacetyl norgestimate in combination with an estrogen |
EP0836506A1 (en) † | 1995-06-07 | 1998-04-22 | Cygnus, Inc. | Transdermal patch and method for administering 17-deacetyl norgestimate alone or in combination with an estrogen |
DE19526864A1 (en) * | 1995-07-22 | 1997-01-23 | Labtec Gmbh | Hormone patches |
US5985311A (en) * | 1995-07-22 | 1999-11-16 | Labtec Gesellschaft Fuer Techologische Forschung Und Entwicklung Mbh | Transdermal hormone patch |
US6086911A (en) * | 1995-12-22 | 2000-07-11 | 3M Innovative Properties Company | Drug delivery device |
US5702720A (en) * | 1995-12-22 | 1997-12-30 | Minnesota Mining And Manufacturing Company | Transdermal device for the delivery of flurbiprofen |
DE19649535A1 (en) * | 1996-11-29 | 1998-06-04 | Lohmann Therapie Syst Lts | Process for the production of a plaster-shaped therapeutic system |
DE19649535C2 (en) * | 1996-11-29 | 2000-02-10 | Lohmann Therapie Syst Lts | Process for the production of a plaster-shaped therapeutic system |
WO1998030203A3 (en) * | 1997-01-13 | 1999-04-22 | Jenapharm Gmbh | Transdermal therapeutic system |
WO1998030203A2 (en) * | 1997-01-13 | 1998-07-16 | Jenapharm Gmbh & Co. Kg | Transdermal therapeutic system |
WO1999066908A1 (en) * | 1998-06-22 | 1999-12-29 | Rottapharm B.V. | Matrix-type transdermal patch for steroid hormones |
DE19829713C1 (en) * | 1998-07-03 | 2000-01-05 | Lohmann Therapie Syst Lts | Therapeutic system with the addition of pearlescent pigments |
WO2000006130A1 (en) * | 1998-07-29 | 2000-02-10 | Lts Lohmann Therapie-Systeme Ag | Estradiol-containing patch for transdermal administration of hormones |
AU762589B2 (en) * | 1998-07-29 | 2003-06-26 | Lts Lohmann Therapie-Systeme Ag | Estradiol-containing patch for transdermal administration of hormones |
WO2002003969A2 (en) * | 2000-07-12 | 2002-01-17 | Hexal Ag | Transdermal therapeutic system for highly dispersed silicon dioxide |
WO2002003969A3 (en) * | 2000-07-12 | 2002-05-23 | Hexal Ag | Transdermal therapeutic system for highly dispersed silicon dioxide |
US8580281B2 (en) | 2008-02-27 | 2013-11-12 | Hisamitsu Pharmaceutical Co., Inc. | Medicated patch |
EP2258355B1 (en) | 2008-02-27 | 2020-01-22 | Hisamitsu Pharmaceutical Co., Inc. | Patch |
DE102010040299A1 (en) | 2010-09-06 | 2012-03-08 | Bayer Schering Pharma Aktiengesellschaft | Transdermal therapeutic systems with crystallization-inhibiting protective film (release liner) |
WO2012031985A1 (en) | 2010-09-06 | 2012-03-15 | Bayer Pharma Aktiengesellschaft | Transdermal therapeutic systems with crystallization-inhibiting protective film (release liner) |
Also Published As
Publication number | Publication date |
---|---|
ATE158181T1 (en) | 1997-10-15 |
PT101019A (en) | 1994-02-28 |
AU712692B2 (en) | 1999-11-11 |
HU227531B1 (en) | 2011-07-28 |
DE59208918D1 (en) | 1997-10-23 |
PT101019B (en) | 1999-10-29 |
NO307644B1 (en) | 2000-05-08 |
CA2120599A1 (en) | 1993-05-13 |
FI942011A (en) | 1994-04-29 |
EP0610357B1 (en) | 1997-09-17 |
ES2106888T3 (en) | 1997-11-16 |
EP0610357A1 (en) | 1994-08-17 |
NO941593D0 (en) | 1994-04-29 |
DE4210711A1 (en) | 1993-05-06 |
JPH07506083A (en) | 1995-07-06 |
DK0610357T3 (en) | 1998-05-11 |
FI942011A0 (en) | 1994-04-29 |
JP3526864B2 (en) | 2004-05-17 |
HU9401257D0 (en) | 1994-08-29 |
AU1652997A (en) | 1997-05-29 |
GR3025237T3 (en) | 1998-02-27 |
HUT72964A (en) | 1996-06-28 |
FI110061B (en) | 2002-11-29 |
CA2120599C (en) | 2003-04-15 |
NO941593L (en) | 1994-04-29 |
AU2895392A (en) | 1993-06-07 |
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